5-Methoxy­methyl-4-phen­oxy-1H-pyrazol-3-ol

Shahani, T.; Fun, H.-K.; Ragavan, R.V.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536809050302

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3249-o3250

doi:10.1107/S1600536809050302

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5-Methoxymethyl-4-phenoxy-1H-pyrazol-3-ol

Tara Shahani,^a Hoong-Kun Fun,^a ^*‡ R. Venkat Ragavan,^b V. Vijayakumar ^b and S. Sarveswari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 18 November 2009; accepted 23 November 2009; online 28 November 2009)

In the title compound, C₁₁H₁₂N₂O₃, the pyrazole ring system is essentially planar [maximum deviation = 0.002 (2) Å] and forms a dihedral angle of 66.93 (9)° with the benzene ring. In the crystal packing, pairs of intermolecular N—H⋯O and O—H⋯N hydrogen bonds connect neighbouring molecules into dimers, generating R₂²(10) and R₂²(8) ring motifs, respectively. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For the biological activity of pyrazoles, see: Genin et al. (2000 ); Hsu et al. (1956 ); Jung et al. (2002 ); Kudo et al. (1999 ); Singh et al. (1978 ); Skipper et al. (1955 ); Storer et al. (1999 ); Tewari & Mishra (2001 ). For pyrazole derivatives, see: Baraldi et al. (2003 ); Brown et al. (2004 ); Duma et al. (2000 ); Heerding (2003 ); Qiao et al. (2003 ); Stamford & Wu (2004 ). For a related structure, see: Goh et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₁H₁₂N₂O₃
M_r = 220.23
Monoclinic, P 2₁ /c
a = 8.8876 (5) Å
b = 10.3031 (5) Å
c = 12.0083 (6) Å
β = 100.917 (3)°
V = 1079.7 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.69 × 0.57 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.934, T_max = 0.983
14470 measured reflections
3433 independent reflections
2373 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.138
S = 1.10
3433 reflections
193 parameters
All H-atom parameters refined
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.91 (2)	1.89 (2)	2.7778 (18)	165.7 (19)
O3—H1O3⋯N1ⁱⁱ	0.92 (2)	1.74 (2)	2.6663 (18)	176 (2)
C3—H3A⋯Cg1ⁱⁱⁱ	0.94 (2)	2.77 (3)	2.73	147.6 (18)
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y, -z; (iii) x-1, y, z. Cg1 is the centroid of the C1–C6 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050302/lh2960sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050302/lh2960Isup2.hkl

checkCIF report

Comment top

Pyrazoles are an important class of heterocyclic compounds and many pyrazole derivatives have a broad spectrum of biological activities such as anti-inflammatory (Singh et al., 1978; Tewari & Mishra, 2001), anti-viral (Genin et al., 2000; Storer et al., 1999), anti-tumor (Hsu et al., 1956; Skipper et al., 1955), and herbicidal (Jung et al., 2002; Kudo et al., 1999) activities. Recently urea derivatives of pyrazole been reported as potent inhibitors of P³⁸ kinase (Duma, 2000), On the other hand, pyrazole derivatives are anti-angiogenic agent (Qiao et al., 2003), A3 adenosine receptor antagonist (Baraldi et al., 2003), neuropeptide YY5 receptor antagonists (Stamford & Wu, 2004) and kinase inhibitor for the treatment of type 2 diabetes, hyperlipidemia and obesity (Brown et al., 2004) as well as thrombopiotinmimetics (Heerding, 2003). Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules play an important role in enhancing their biological activity, we are interested to have 4-fluoro and 4-chloro substituted phenyl rings in the aromatic part of a 1,5-diaryl pyrazole. As part of our on going research programme aiming at the synthesis of new anti-microbial compounds, herein we report the crystal structure of a novel pyrazole derivative.

In the crystal structure (Fig. 1), the pyrazole ring system (C7/C8/N2/N1/C11) is approximately planar, with a maximum deviation of 0.002 (2) Å for atom C11. The dihedral angle formed between the mean plane of pyrazole ring and the benzene ring (C1–C6) is 66.93 (9)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to a closely related structure (Goh et al., 2009).

In the crystal packing (Fig. 2), pairs of intermolecular N2—H1N2···O2ⁱ and O3—H1O3···N1ⁱⁱ hydrogen bonds (Table 1) connect neighbouring molecules, into dimers, generating R₂²(10) and R₂²(8) ring motifs (Bernstein et al., 1995), respectively. The crystal structure is further stabilized by C—H···π interactions (Table 1), involving the C1–C6 (centroid Cg1) benzene ring.

Related literature top

For the biological activity of pyrazoles, see: Genin et al. (2000); Hsu et al. (1956); Jung et al. (2002); Kudo et al. (1999); Singh et al. (1978); Skipper et al. (1955); Storer et al. (1999); Tewari & Mishra (2001). For pyrazole derivatives, see: Baraldi et al. (2003); Brown et al. (2004); Duma et al. (2000); Heerding (2003); Qiao et al. (2003); Stamford & Wu (2004). For a related structure, see: Goh et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C1–C6 benzene ring.

Experimental top

LiHMDS (19.4 ml, 1.0 min THF, 19.4 mmol) was added quickly to the solution of oxyacetic acid ethyl ester (1.0 g, 5.5 mmol) in toluene (15.0 ml) using syringe at 195 K with agitation and the anion formed was allowed to stand for approximately 1 min, and then 2-methoxyacetyl chloride (1.0 ml, 13.8 mmol) was added into the lot with stirring. Reaction mixture was removed from acetone-dry ice bath and stirred for 10 min then acetic acid (2.0 ml) was added with stirring. Ethanol (15.0 ml) and hydrazine hydrate (1.5 ml, 44.0 mmol) was added and refluxed for 10 min. Reaction mixture was concentrated to dryness under reduced pressure and redissolved in ethyl acetate. The organic layer was washed with saturated brine solution, dried over Na₂SO₄ and evaporated under reduced pressure. Crude product was purified by column chromatography using a mixture of 1:99 methanol and ethylacetate. Pale yellow solid was obtained. Mp. 418.8–419.8 K. Yield: 57%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along a axis. Intermolecular hydrogen bonds are shown by dashed lines.

5-Methoxymethyl-4-phenoxy-1H-pyrazol-3-ol top

Crystal data top

C₁₁H₁₂N₂O₃	F(000) = 464
M_r = 220.23	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6087 reflections
a = 8.8876 (5) Å	θ = 2.3–32.2°
b = 10.3031 (5) Å	µ = 0.10 mm⁻¹
c = 12.0083 (6) Å	T = 100 K
β = 100.917 (3)°	Plate, yellow
V = 1079.7 (1) Å³	0.69 × 0.57 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3433 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 31.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→11
T_min = 0.934, T_max = 0.983	k = −14→14
14470 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	All H-atom parameters refined
S = 1.10	w = 1/[σ²(F_o²) + (0.0465P)² + 0.7446P] where P = (F_o² + 2F_c²)/3
3433 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₁H₁₂N₂O₃	V = 1079.7 (1) Å³
M_r = 220.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8876 (5) Å	µ = 0.10 mm⁻¹
b = 10.3031 (5) Å	T = 100 K
c = 12.0083 (6) Å	0.69 × 0.57 × 0.18 mm
β = 100.917 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3433 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2373 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.983	R_int = 0.032
14470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.138	All H-atom parameters refined
S = 1.10	Δρ_max = 0.45 e Å⁻³
3433 reflections	Δρ_min = −0.33 e Å⁻³
193 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.79382 (13)	0.20467 (12)	0.25817 (9)	0.0209 (3)
O2	0.84461 (13)	0.54359 (11)	0.06550 (11)	0.0243 (3)
O3	0.86330 (14)	−0.01790 (11)	0.10686 (10)	0.0210 (3)
N1	0.97188 (15)	0.15166 (12)	0.01762 (11)	0.0187 (3)
N2	0.98156 (16)	0.28291 (13)	0.03420 (12)	0.0197 (3)
C1	0.5751 (2)	0.2793 (2)	0.32287 (16)	0.0313 (4)
C2	0.4180 (2)	0.2854 (2)	0.31444 (19)	0.0373 (5)
C3	0.3212 (2)	0.2243 (2)	0.22663 (17)	0.0315 (4)
C4	0.3817 (2)	0.1569 (2)	0.14638 (17)	0.0339 (4)
C5	0.5396 (2)	0.1508 (2)	0.15308 (16)	0.0293 (4)
C6	0.63487 (18)	0.21173 (15)	0.24200 (13)	0.0182 (3)
C7	0.85883 (17)	0.21114 (15)	0.16285 (13)	0.0178 (3)
C8	0.91537 (18)	0.32155 (15)	0.12032 (13)	0.0188 (3)
C9	0.9123 (2)	0.46065 (16)	0.15618 (14)	0.0222 (3)
C10	0.6866 (2)	0.51602 (19)	0.02363 (19)	0.0310 (4)
C11	0.89717 (17)	0.10779 (15)	0.09653 (13)	0.0177 (3)
H1A	0.644 (3)	0.324 (2)	0.3821 (19)	0.042 (6)*
H2A	0.375 (3)	0.334 (3)	0.368 (2)	0.056 (8)*
H3A	0.214 (3)	0.227 (2)	0.2222 (19)	0.039 (6)*
H4A	0.315 (3)	0.112 (3)	0.087 (2)	0.050 (7)*
H5A	0.583 (2)	0.106 (2)	0.0976 (18)	0.033 (6)*
H9A	1.017 (2)	0.4927 (19)	0.1791 (16)	0.021 (5)*
H9B	0.853 (2)	0.466 (2)	0.2184 (17)	0.028 (5)*
H10A	0.678 (2)	0.428 (2)	−0.0107 (19)	0.038 (6)*
H10B	0.652 (3)	0.582 (3)	−0.032 (2)	0.047 (7)*
H10C	0.625 (3)	0.518 (2)	0.088 (2)	0.041 (6)*
H1N2	1.038 (2)	0.329 (2)	−0.0073 (17)	0.024 (5)*
H1O3	0.924 (3)	−0.065 (2)	0.067 (2)	0.047 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0193 (5)	0.0261 (6)	0.0184 (5)	0.0006 (5)	0.0062 (4)	−0.0018 (4)
O2	0.0232 (6)	0.0139 (6)	0.0362 (7)	−0.0005 (4)	0.0070 (5)	0.0036 (5)
O3	0.0265 (6)	0.0133 (5)	0.0264 (6)	−0.0028 (5)	0.0134 (5)	−0.0010 (4)
N1	0.0228 (7)	0.0116 (6)	0.0232 (6)	0.0002 (5)	0.0081 (5)	0.0000 (5)
N2	0.0233 (7)	0.0131 (6)	0.0246 (7)	−0.0006 (5)	0.0091 (5)	0.0009 (5)
C1	0.0302 (9)	0.0340 (11)	0.0320 (9)	−0.0006 (8)	0.0114 (7)	−0.0121 (8)
C2	0.0321 (10)	0.0416 (12)	0.0431 (11)	0.0074 (9)	0.0194 (9)	−0.0070 (9)
C3	0.0215 (8)	0.0372 (11)	0.0378 (10)	0.0046 (8)	0.0110 (7)	0.0117 (8)
C4	0.0228 (9)	0.0446 (12)	0.0332 (10)	−0.0023 (8)	0.0027 (7)	−0.0019 (9)
C5	0.0236 (9)	0.0364 (11)	0.0286 (9)	0.0012 (7)	0.0065 (7)	−0.0094 (8)
C6	0.0198 (7)	0.0143 (7)	0.0220 (7)	0.0012 (6)	0.0080 (6)	0.0024 (6)
C7	0.0187 (7)	0.0175 (7)	0.0178 (7)	0.0007 (6)	0.0051 (5)	−0.0002 (6)
C8	0.0191 (7)	0.0154 (7)	0.0218 (7)	0.0013 (6)	0.0038 (6)	−0.0012 (6)
C9	0.0254 (8)	0.0153 (8)	0.0263 (8)	0.0004 (6)	0.0056 (6)	−0.0022 (6)
C10	0.0238 (9)	0.0213 (9)	0.0462 (11)	0.0011 (7)	0.0020 (8)	0.0031 (8)
C11	0.0181 (7)	0.0159 (7)	0.0198 (7)	−0.0007 (6)	0.0054 (5)	0.0001 (6)

Geometric parameters (Å, º) top

O1—C7	1.3781 (18)	C3—C4	1.377 (3)
O1—C6	1.3910 (19)	C3—H3A	0.94 (2)
O2—C9	1.425 (2)	C4—C5	1.392 (3)
O2—C10	1.427 (2)	C4—H4A	0.96 (3)
O3—C11	1.3406 (19)	C5—C6	1.382 (2)
O3—H1O3	0.92 (3)	C5—H5A	0.95 (2)
N1—C11	1.335 (2)	C7—C8	1.380 (2)
N1—N2	1.3672 (19)	C7—C11	1.410 (2)
N2—C8	1.343 (2)	C8—C9	1.498 (2)
N2—H1N2	0.91 (2)	C9—H9A	0.98 (2)
C1—C6	1.380 (2)	C9—H9B	0.99 (2)
C1—C2	1.383 (3)	C10—H10A	0.99 (2)
C1—H1A	0.96 (2)	C10—H10B	0.96 (3)
C2—C3	1.380 (3)	C10—H10C	1.03 (2)
C2—H2A	0.95 (3)

C7—O1—C6	117.13 (12)	C1—C6—O1	116.36 (15)
C9—O2—C10	113.24 (13)	C5—C6—O1	122.80 (14)
C11—O3—H1O3	107.0 (15)	O1—C7—C8	125.92 (14)
C11—N1—N2	104.93 (13)	O1—C7—C11	128.09 (14)
C8—N2—N1	112.37 (13)	C8—C7—C11	105.64 (14)
C8—N2—H1N2	129.8 (13)	N2—C8—C7	106.50 (14)
N1—N2—H1N2	117.5 (13)	N2—C8—C9	122.63 (14)
C6—C1—C2	119.29 (18)	C7—C8—C9	130.87 (15)
C6—C1—H1A	119.0 (14)	O2—C9—C8	112.47 (13)
C2—C1—H1A	121.7 (14)	O2—C9—H9A	104.7 (11)
C3—C2—C1	120.65 (18)	C8—C9—H9A	109.7 (11)
C3—C2—H2A	119.0 (16)	O2—C9—H9B	109.6 (12)
C1—C2—H2A	120.3 (16)	C8—C9—H9B	107.9 (12)
C4—C3—C2	119.72 (17)	H9A—C9—H9B	112.5 (16)
C4—C3—H3A	119.8 (14)	O2—C10—H10A	108.6 (13)
C2—C3—H3A	120.5 (14)	O2—C10—H10B	105.4 (14)
C3—C4—C5	120.34 (18)	H10A—C10—H10B	111.7 (19)
C3—C4—H4A	119.9 (15)	O2—C10—H10C	111.1 (13)
C5—C4—H4A	119.7 (15)	H10A—C10—H10C	108.8 (18)
C6—C5—C4	119.20 (17)	H10B—C10—H10C	111.3 (19)
C6—C5—H5A	119.6 (13)	N1—C11—O3	122.92 (14)
C4—C5—H5A	121.2 (13)	N1—C11—C7	110.57 (14)
C1—C6—C5	120.79 (16)	O3—C11—C7	126.51 (14)

C11—N1—N2—C8	−0.09 (17)	N1—N2—C8—C9	179.33 (14)
C6—C1—C2—C3	0.3 (3)	O1—C7—C8—N2	173.96 (14)
C1—C2—C3—C4	−0.2 (3)	C11—C7—C8—N2	0.26 (17)
C2—C3—C4—C5	−0.4 (3)	O1—C7—C8—C9	−5.4 (3)
C3—C4—C5—C6	0.9 (3)	C11—C7—C8—C9	−179.12 (16)
C2—C1—C6—C5	0.2 (3)	C10—O2—C9—C8	64.02 (19)
C2—C1—C6—O1	−177.32 (17)	N2—C8—C9—O2	56.1 (2)
C4—C5—C6—C1	−0.7 (3)	C7—C8—C9—O2	−124.58 (18)
C4—C5—C6—O1	176.57 (17)	N2—N1—C11—O3	179.16 (14)
C7—O1—C6—C1	−142.80 (16)	N2—N1—C11—C7	0.26 (17)
C7—O1—C6—C5	39.8 (2)	O1—C7—C11—N1	−173.85 (14)
C6—O1—C7—C8	95.50 (18)	C8—C7—C11—N1	−0.33 (18)
C6—O1—C7—C11	−92.22 (19)	O1—C7—C11—O3	7.3 (3)
N1—N2—C8—C7	−0.12 (18)	C8—C7—C11—O3	−179.19 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.91 (2)	1.89 (2)	2.7778 (18)	165.7 (19)
O3—H1O3···N1ⁱⁱ	0.92 (2)	1.74 (2)	2.6663 (18)	176 (2)
C3—H3A···Cg1ⁱⁱⁱ	0.94 (2)	2.77 (3)	2.73	147.6 (18)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y, −z; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₂O₃
M_r	220.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.8876 (5), 10.3031 (5), 12.0083 (6)
β (°)	100.917 (3)
V (Å³)	1079.7 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.69 × 0.57 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.934, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	14470, 3433, 2373
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.725

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.138, 1.10
No. of reflections	3433
No. of parameters	193
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.91 (2)	1.89 (2)	2.7778 (18)	165.7 (19)
O3—H1O3···N1ⁱⁱ	0.92 (2)	1.74 (2)	2.6663 (18)	176 (2)
C3—H3A···Cg1ⁱⁱⁱ	0.94 (2)	2.77 (3)	2.73	147.6 (18)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y, −z; (iii) x−1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

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